Synthesis of alpha-Alkynyl- and Aziridinyl-phosphonates from alpha-Phosphonovinyl Triflates
Disciplines
Chemistry | Organic Chemistry | Physical Sciences and Mathematics
Abstract (300 words maximum)
Alpha-phosphonovinyl triflates are a novel class of phosphonates that have been developed in our lab. We are exploring their chemical nature and have been successful in widening the synthetic scope of these molecules. For example, we have successfully used them as substrates in organopalladium catalyzed reactions to prepare alpha, beta-functionalized vinylphosphonates. Recently, we have developed a method to prepare alpha-alkynylphosphonates via a base promoted E2 reaction. Additionally, the triflates have been reacted with amines to afford alpha-aziridinylphosphonates via a Gabriel-Cromwell reaction. Interestingly, we have observed competing E2 and Gabriel-Cromwell reactions depending on the amine used. A summary of our method to synthesize alpha-alkynylphosphonates and alpha-aziridinylphosphonates from alpha-phosphonovinyl triflates will be presented.
Academic department under which the project should be listed
CSM - Chemistry and Biochemistry
Primary Investigator (PI) Name
Christopher W. Alexander
Synthesis of alpha-Alkynyl- and Aziridinyl-phosphonates from alpha-Phosphonovinyl Triflates
Alpha-phosphonovinyl triflates are a novel class of phosphonates that have been developed in our lab. We are exploring their chemical nature and have been successful in widening the synthetic scope of these molecules. For example, we have successfully used them as substrates in organopalladium catalyzed reactions to prepare alpha, beta-functionalized vinylphosphonates. Recently, we have developed a method to prepare alpha-alkynylphosphonates via a base promoted E2 reaction. Additionally, the triflates have been reacted with amines to afford alpha-aziridinylphosphonates via a Gabriel-Cromwell reaction. Interestingly, we have observed competing E2 and Gabriel-Cromwell reactions depending on the amine used. A summary of our method to synthesize alpha-alkynylphosphonates and alpha-aziridinylphosphonates from alpha-phosphonovinyl triflates will be presented.